磷酸二氢钾催化Yonemitsu缩合反应合成5-[(3-吲哚基)-芳甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮衍生物

doi:10.11944/j.issn.1000-0518.2015.12.150165

摘要/Abstract

摘要：

以醛、吲哚和麦氏酸为原料,水和乙醇混合液为溶剂,在室温搅拌条件下以磷酸二氢钾为催化剂通过Yonemitsu缩合反应,合成了一系列的5-[(3-吲哚基)-芳甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮衍生物,产率为48%~98%,并通过X射线单晶衍射仪测定了化合物4o的晶体结构。该方法能够有效的促使反应活性较低的4-甲基苯甲醛和4-甲氧基苯甲醛参与反应,以83%和60%的收率获得相应的目标产物,并具有反应条件温和、催化剂廉价易得、后处理简单、产物易于纯化、产率较高等优点,可用于合成3-取代吲哚类化合物。

关键词: 三组分反应, Yonemitsu缩合反应, 磷酸二氢钾, β-取代吲哚衍生物, 合成

Abstract:

A simple and efficient procedure for the preparation of 5-[(indol-3-yl)-arylmethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives has been developed through the Yonemitsu condensation of indole with Meldrum's acid and aldehyde in the mixed solvent of ethanol and water at room temperature using KH₂PO₄ as an inexpensive, commercially available, and efficient catalyst. The crystal structure of compound 4o was confirmed by X-ray diffraction. This method has the advantages of mild reaction conditions, tolerance to diverse functional groups such as 4-methyl benzaldehyde and 4-methoxy benzaldehyde, and good to excellent yields(48%~98%). Furthermore, some of the products can be facilely obtained by vacuum filtration without further purification. This strategy provides an alternative approach for easy access to useful synthetic β-indole derivatives.

Key words: three-component reaction, Yonemitsu condensation, potassium dihydrogen phosphate, β-indole derivatives, synthesis

吕成伟, 刘妍杭, 王佳晶, 周晓霞. 磷酸二氢钾催化Yonemitsu缩合反应合成5-[(3-吲哚基)-芳甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮衍生物[J]. 应用化学, 2015, 32(12): 1371-1378.

LYU Chengwei, LIU Yanhang, WANG Jiajing, ZHOU Xiaoxia. Potassium Dihydrogen Phosphate Catalyzed Yonemitsu Condensation for Synthesis of 5-[(Indol-3-yl)-arylmethyl]-2,2-dimethyl-1,3-dioxane- 4,6-dione Derivatives[J]. Chinese Journal of Applied Chemistry, 2015, 32(12): 1371-1378.

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